Concise total synthesis of (-)-deoxocuscohygrine and (-)-dihydrocuscohygrine.
The concise enantioselective total synthesis of C(2)-asymmetrical (-)-deoxocuscohygrine and (-)-dihydrocuscohygrine are described. Double-diastereoselective additions of normal Grignard reagent to bis(1,3-oxazolidine) have been deployed to construct chiral diamine fragments as a key step.
Yamauchi
Takayasu
T
Institute of Medicinal Chemistry, Hoshi University, Ebara, Shinagawa, Tokyo 142-8501, Japan. yamauchi@hoshi.ac.jp
Hagiwara
Sachi
S
Higashiyama
Kimio
K
D000096:Acetone / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D011759:Pyrrolidines / Q000138:chemical synthesis*; D013055:Spectrophotometry, Infrared
D007202:Indicators and Reagents; D011759:Pyrrolidines; C543793:deoxocuscohygrine; C472459:dihydrocuscohygrine; D000096:Acetone